5,5′-(p-Phenylene)di-1H-tetrazole

Abstract

Crystals of the title organic compound, C8H6N8, were generated in situ through the [2 + 3]-cyclo-addition reaction involving the precursor 1,4-dicyano-benzene and azide in water with Zn2+ as Lewis acid. The asymmetric unit consists of one half-mol-ecule, and a twofold axis of symmetry passes through the centre of the benzene ring. There is an inter-molecular N - H⋯N hydrogen bond. The mol-ecules are assembled into a three-dimensional supra-molecular framework by π-π stacking inter-actions, with a perpendicular distance of 3.256 Å [centroid-centroid = 3.9731 (8) Å] between two tetra-zole ring planes, and 3.382 Å between the benz-ene ring and tetra-zole ring planes [centroid-centroid = 3.5010 (9) Å]. © International Union of Crystallography 2008.